Ep. 25: What the First Year of Entrepreneurship is REALLY Like (no B.S.)

Today is so, so special and so personal to me. And no, I'm not talking about dating this week. I am talking about entrepreneurship because I'm celebrating one year as an entrepreneur. My business, The Happy Marketing Co., is turning one today on February 1st, 2024.

It's hard to believe, honestly, that it's been a whole year because I remember this time last year having a way different experience. I was feeling a little bit excited about starting a business, but I was definitely overwhelmed and stressed and completely unaware of what was ahead for me. And if you don't know my story, I gave 30 days notice during Christmas season in 2022.

Little did I know I was giving notice from my last corporate job. I was feeling terrified. I kept applying for jobs with like no offers or just no good fit for me. And so I started freelancing because I was like, well, I have to start making money. And I started realizing maybe I could make a business out of it.

And I don't know where you're at in your career. But when you start to realize that there could be something else for you in your journey, it kind of gets exciting, but also terrifying. But I decided one year ago to take the biggest risk I've ever taken on myself and officially launch a business.

I got an LLC. I announced it on social media. I designed a website. And I launched The Happy Marketing Co. as a marketing consultancy. I was like, whatever you need for marketing, social media, email, website, SEO, I'm your girl. And now that it's been a year later, so much has changed.

But I first want to say, that if you have an idea for a business, or maybe you're in your first year of business, or in your side hustle, or even if you're trying to grow an existing business right now, I truly want to let you know, it's not only possible to replace your full time income, but you can actually make more. Be happy, find fulfillment, and have tons of flexibility in your life. But let's get real for a second. Because in life, for me as a person, and on The Happy Leader podcast, and especially in this episode, I am going to give you the no-bullshit answers to the topics and the questions that I'm going to go through. So I just want to put that out there. I'm going to be completely honest with you. No bullshit, I promise.

In today's episode, I'm going to give you a rundown of what year one looks like when you're starting the business. The raw, the happy, the emotional, the freaking stressed out. Again, the no-bullshit answer. Because I worked so freaking hard. And I almost gave up a few times, like, seriously, I was like looking for full-time jobs at some point. And I was so scared that this wasn't going to work out. And I'm going to be super, super transparent with you.

I actually lost a client the day that I recorded this episode, which I recorded this episode on the eve of the anniversary. So on January 31st, I lost a client and they were one of my first clients. So it's kind of funny how we're about to celebrate our first year working together and I lost them as a client, but to be honest, I knew it was coming and to be even more honest, this client — I love so much. I love the business. I love the people. I've loved being a part of their team from a distance, but because my business has evolved so much this year, and I'm not just talking about with revenue and all of that, because my services have changed because I've learned about who I am as an entrepreneur.

And I've also learned what I really want to offer in my business. I knew for a few months that this partnership was no longer a fit for me, but I was hanging onto it because it's revenue because I'm still in my first year of business. I needed that safety. I needed to have this client. In the last few months, which I'm going to talk about in a few minutes, they've been pretty stressful.

Through the holidays, through having COVID and being out sick for three weeks, it's been a journey for me. But Because of what happened this week and because of my experience in the past year, I wanted to record this super raw and honest conversation because I know a lot of you who are interested in starting the business or who are hanging on to the business they have right now, or maybe you want to do something completely different.

You're like, I just need someone to tell me if it's possible, or I just need someone to tell me how I can make this work. I'm going to help you through that today because again, like I needed this kind of support when I first launched my business and I honestly didn't find it right away. I was looking in so many places, so many communities, so many memberships, and on social media. And I just kind of got stuck in my head for a really, really long time. And so what I want to do today is kind of clear up some of the confusion that comes with starting the business and becoming an entrepreneur for the first time, but I'm also going to get.

I'm going to share my perspective as a business owner who is a marketing consultant, one who didn't really tap into passive income or even know what that was for my own business until very recently. And one who did it the organic way. I didn't run ads. I wasn't sharing these get-rich-quick Reels on Instagram, anything like that. I really did it this raw, organic way. And I've learned so much. And yes, I'm still learning because I'm only one year in, but what shocks me is I'm one year in and I still hit six figures in my first year.

And I looked back today and I actually hit my first five-figure month in only four months. And so maybe I'm sharing that, but I definitely did not get rich quick. I did it the organic way. I did it by reaching out to clients by getting referrals, by doing a ton of work for not a lot of money. I kind of played it the hard way.

And so that's why I want to share this episode too, because I want to share what I did wrong maybe, or what I learned from doing certain things. But I also want to share like. Now that I know kind of what happened in the last year, I want to share everything that I'm so proud of and everything that I've learned.

Here are the five biggest aspects of jumping into entrepreneurship and starting a business.

Starting a new routine

I've worked in corporate for most of my career, like literally 13, 14 years. And when I quit corporate, I started my own business and I was contracting and consulting. One of the biggest areas that I struggled with was finding a new routine. And it was so weird to me that I didn't have to check in with someone every morning. I didn't have to jump on a call or a meeting first thing.

And it was so different for me. I'm used to, you know, having a boss who's like, “Lindsay, can you tell me where this is at? Or we're going to have a team meeting or can you jump on a call right now?” I'm used to kind of being in the moment by having a boss. And so, yeah, like having a new routine was foreign to me.

And something that I had to do was create a routine. I definitely took a few weeks off and I was like, I'm going to refresh. I did a ton of interviews, like a shit-ton of interviews. I think I had 20, 25 interviews. It was intense. But I was like, okay, my calendar is either super full with interviews or I have nothing to do.

So I had to create a routine and literally time block my calendar. Do you remember when we were kids and we had that little board on our wall? And it was like, brush your teeth or make your bed. And you would get a little star sticker. I don't know, but I did that when I was a kid. And I feel like I had to do that for myself while becoming an entrepreneur because I, again, had so much flexibility, but at the same time, no one to keep me accountable.

So if you're an entrepreneur now, or you're going to become an entrepreneur, I definitely recommend putting a little bit of time into creating a new routine because no one is going to keep you accountable like you will. So put it in your calendar, write it on your fridge or put it on a whiteboard. Give yourself a star for everything you have to do in one day.

But this really helps me kind of find my new way while also having the flexibility and going to brunch in the middle of the day, whatever I wanted to do, but I still held myself accountable. And I had to ease into it because I was going to have all these new clients soon. So the more of a routine I could start now, the better easing into that was going to be.

Figuring out which services to offer

If I'm being completely honest with you, I kind of had a set of services before I launched the business because I needed it on my website and all of that. But I really didn't figure this out until I was in the business, until I was in the day to day, until I signed clients on and got some good experience in. Because for me having all this marketing experience, I was like, I'm going to be a consultant and I'm going to have marketing retainers and I'm going to do whatever clients want because I just need to get clients. So I wore all the hats in marketing.

And what happened was I started to get clients through referrals and networking and all the things, but I kind of went from having one boss to like five bosses. And I was like, what the hell am I doing? Like now I'm even more stressed out. I'm even more burned out. I'm getting all these text messages and emails and this is just not working for me. So although the first probably six months of business, I was offering social media, email, marketing, SEO, websites, ads, like all these things, I had to realize it's okay to niche down. And I think when a lot of us hear that we're like…nope, I'm not going to niche down. That's stupid. Like, I don't even know what a niche is.

But for me, it was the best decision that I've made in my business, honestly, because now I'm only offering the services that I'm obsessed with — the services that I know will make me money and the services that I know will help my clients. But that doesn't mean I have to offer all the services. Something that one of my mentors told me is, if I'm offering everything to every client out there, I'm not going to be known for anything. And I truly believe that because now I get so many referrals for SEO services. And even when I'm on a networking call, for example, if I say I'm Lindsay, I own The Happy Marketing Co. and I offer SEO services, then people are like, okay, that's the SEO girl.

So if they realize that they need SEO services or they know someone who is, then I'm their girl. And if you keep hearing me say SEO and you aren't sure what that means, it's search engine optimization. And basically I just work some magic with keywords, with your links, with your website content, and I get your business on the first page of Google. So it's a really exciting experience. It's very technical and it's really complex, but I love SEO. And honestly, there's not a lot of females in SEO. So I'm like, I'm going to rock this and it's a little bit scary, but you know what, I'm doing the dang thing because now I'm known for it and I love that. So I had to figure out what services to offer.

Wherever you're at in your business, if you feel like, I'm offering so many services and I just can't keep track or I'm doing all these things that I don't really want to do, then maybe it's time to niche down just a little bit.

Gaining clients, losing clients, and firing clients

So again, this might make you feel a little bit hot in your chest. Like, I'm a little bit anxious as I'm talking about this. If you can't tell, I feel like my voice just got really fast. So let's slow it down. So gaining clients, this is really important, right? As you're growing your business, you need new clients.

And as I just mentioned, I niched down my services. So I stopped working with all the clients. And there were a lot of clients who were like, I just need social media or I just need email. And the first couple of times that I had to say on discovery calls or in meetings, like actually “I don't offer social media, I don't offer email…” it was really scary and it was really hard, but a lot of those clients actually came back and they wanted SEO. They wanted a new website designed or they needed their existing website to be optimized or edited or whatever. So it made me so nervous. But again, like I gained the right clients when I niched down and it just gave me more to talk about.

It gave me more in terms of the work I was doing for these clients. I got to share that with people. I got to share that on social media and it just felt like a much better balance for me. So gaining clients, obviously super important.

Now let's talk about losing clients, which as you heard earlier, I did lose a client, but here's the thing again, I want to make sure that I'm serving my clients the best I can. And this client that I had, even though I loved them so much and I really did support their cause and all the things, they weren't a fit for me anymore. Because as I just said, I niched down and I was offering everything for this client. I was offering social media, email, PR, website edits, all these things.

And even though I wanted to hang on to them, it wasn't a fit for where I want to go. And so that was like kind of a hard pill to swallow at first when I was like, I just got like broken up with. But it was the right move. And I think it was honestly the universe and the inner Lindsay who's like, “This is what you wanted, but you were just too chicken to actually, you know, quit this account.” But things happen for a reason. And I know that whoever they bring on is going to be a better fit because they're going to really want to offer all those services. And that's just not aligned for me anymore.

If I can also offer another piece of advice, I was terrified to lose clients this whole year. And it is really scary, right? Because you don't have a consistent paycheck. So when you have a retainer client, you really rely on them. I am really excited to have some SEO retainer clients, but I want you to know this. Yes, it really, truly sucks to lose a client and it's really, really stressful, especially in your first year, but things happen for a reason. And I truly believe that. And I'm not saying the second you lose a client, just go manifest a new client coming along. But this week alone, I got to jump on a call with someone who's like really interested in working with me long term and another client who's like, let's book a call, I'm really interested.

So I'm just here to say that losing one client is not going to be the end of the world. And if you're hanging on to one client, because you need every dollar of that income, there's a lot you can do to make that up. You can create some digital products, you can create a course, and you can get on social media and have a sale on one of your services. There's a lot you can do. So I just don't want it to feel like the end of the world when you lose a client and maybe just like a breakup, maybe you have a quick cry or you go for a walk and you, you know, get the anger or the anxiety out of you. But then show back up in your business because one client is not going to make or break your business and a year ago I probably wouldn't have said that but I know that it's true now.

All right, the last point I want to say in number three is firing clients. I know this kind of sounds aggressive, but let me tell you this quick story. So about six months into my business, I had this client that I just knew wasn't a fit for me but I needed the income and I wanted the challenge and I wanted the experience. But I just I knew they weren't a fit for me. I was actually on a trip, and I let them know that I was on a trip. I was out of office for the week and if they wanted to schedule a call, we could do it next week, but everything was running smoothly. There weren’t any projects due that week. And they started texting me while I was out. They sent me emails, they texted me. And one of the emails that they said was, “Hey, let's jump on a call tomorrow.” And I was like, “I'm still on my trip.” And I was actually out to dinner with a bunch of women and they could just see my face. I started to freak out and I seriously started having a panic attack in the restaurant. Like physically I started having a panic attack. It was probably the quietest panic attack that I've ever had because I was sitting at the table in the middle of a bunch of women, but it was awful.

I just remember that feeling of like, what am I supposed to do? I have to jump on a call. Like I'm going to have to, you know, not go to an event tomorrow or make it work. And I was talking to my mentor who was there and she was like, “They know that you're out of office. This is a trigger for you because you came from corporate and that happened a lot.”

Like I would get texted in the middle of the night or one time I got in trouble for going to bed at 8 PM. That's another story, but like, I was definitely triggered and she just helped me remember that this is why I started my business because I didn't want to feel that way anymore. I didn't want to get text messages in the middle of the night or while I'm on a trip. I didn't want to be controlled by a client anymore. I didn't want to be controlled by a boss anymore. I wanted to own my power. And so she was like, “Put your phone away. Don't respond to it right now.” And so I did that. I put my phone away and I about to cry or scream or something in that restaurant, but I did respond later.

And I was like, “Hey, as I mentioned, I'm on a trip. We can schedule a call next week. Here's my calendar link, but I'm on a trip and I'm no longer answering email.” And that was so hard for me. And what did end up happening was I had to release them. I knew that they would keep triggering me and I just knew it wasn't a good fit.

And again, this one client did not break my business, even though I felt like it was going to. But I had to release them and it felt so freaking good to no longer work with them. And I love these people. I love their business, but sometimes you meet people that you're just not supposed to work with and that's okay.

Joining a community and investing in coaching

I wanted to share this one because I feel like this is kind of like the thing to do now when you're an entrepreneur, when you have a business is to invest in a coach, so I wanted to talk about this real quick. So first of all joining a community — I actually think this is really important. And I'm going to tell you why I think it's important when you're an entrepreneur, because if you're like me and you came from corporate, that's kind of all you know, right?

Joining the community of other female entrepreneurs was so cool to meet other women that were doing the same thing as me, even if they were in month one or year 10. It was just so cool to be around a group of women. So I definitely recommend that you join a community wherever you're at…if you're doing the side hustle, if you're about to leave corporate, if you're already a year into your business and it just kind of feels lonely, find a community. There's so many different communities out there, and it doesn't have to just be females or whatever, but find a community. Try out like at least three, because I jumped into my first community and I loved it and I met a lot of amazing people who I'm still friends with. But I actually started going to some other communities recently, and I feel like they're much better match for me when it comes to the goals that I have and where I want to take my business.

A couple other things that I want to mention with community is number one, you have to not compare yourself to other women. And I'm still telling this to myself because as soon as I joined a community with other entrepreneurs, I was comparing my business to them. I was comparing my outfits to them and where they were in life, all these things, and you just can't do that. You're in completely different phases of your life and your business.

And it's just not fair to put that pressure on someone to put that pressure on yourself. So please, whatever you do, don't go into a room and compare yourself to every woman out there. And don't do that on Instagram. And if you feel like you are doing that on social media, maybe just start unfollowing some people or maybe mute them. I've definitely had to do that because I just can't have that in my ecosystem every day. I just can't be watching people that I get jealous of or that have really good ideas and it kind of makes me bitter. I just can't do that to myself. So I had to unfollow and mute a lot of people and that's okay. They're never gonna know but you need to join a community for yourself, one where you feel really comfortable in and one that you just feel like you're a part of like, truly, it's not like a comparison and anything like that. I will say that it's really important to join a community where there are people who are in the same phase of business as you, but there are also people who are like 10 steps ahead where you're like, “I want to be just like them. Like they're my big inspo.”

You definitely want to get in the room with those kinds of people because they will inspire you. They will push you. They will give you such good advice and you definitely need that in your life. And the last thing I want to say about community and friendships when you're in this new phase of entrepreneurship is you have to stay invested in your friendships that are outside of entrepreneurship. And this is huge because I have so many friends who are not entrepreneurs, but I love them. Like I went to high school with them. I went to college with them. I even just met my best friend like two years ago. You have to stay invested in those friendships too. And you can keep them a little bit separate.

I'm sure your friends who work in corporate or are stay at home moms, I'm sure they don't want to hear about business all the time, but yes, like they should check in with you and they should encourage you and all of that. But keep your friendships because even though you just became an entrepreneur, that doesn't mean that you only have to hang out with entrepreneurs. So just keep friendships a little bit balanced and don't change too much all at once.

I just want to touch on the coaching part. So I feel like a lot of times we're encouraged to invest in our business and invest in ourselves. And I definitely agree with that to some degree. But when I started making a little bit of money in my business, I was like looking for somewhere to spend it. I was like, “Oh, now I'm supposed to invest in a coach or invest in a program or join a mastermind, whatever.” And so I joined a marketing membership right away. And it was $650 a month. And that was a lot. Like, I feel like that's still a lot when you're starting out in a business, if it's definitely going to help you pivot forward and answer a lot of questions and help you grow your business, then it's not a huge investment.

But this was like a year's worth of $650 payments. Then I started realizing right away, I did not look into everything that was involved. So if you are going to invest in something, definitely look into it a little bit more, like have a call with someone or just figure out like, is this right for me? Like, what am I struggling with the most right now? And that's where you need to go invest. If you're struggling with sales, you need to invest in a sales program or a sales mentor or a course about sales. If you're struggling with money mindset, then definitely put some money toward that. That could even mean reading a really good book. And my go to book is “You're a badass at making money.” So when you're kind of in this phase of like growth or where do I invest…just take some time because you don't have to just waste your time. So just do a lot of research and feel it out.

The ups and downs of revenue

As I mentioned, I did hit six figures in my first year, which I'm so thankful for. I'm really proud of that and I worked really hard to hit over six figures and I worked really hard to get to my first five-figure month in only four months. But here's the deal, especially in your first year of business…you are on a freaking rollercoaster.

Like seriously, I remember getting all these new clients right away and I was like, holy shit, I'm going to be a millionaire by the end of the year. And obviously that didn't happen, but it's a rollercoaster and you never know what the next month is going to look like. And yes, having a retainer based program for clients where maybe it's a three month commitment or a six month or 12 month program that really does help you kind of forecast what the year is going to look like, what the quarter is going to look like.

So I definitely recommend kind of looking at that, but things happen. The one client that I had to let go and completely disconnect from, it was a really good contract for me, but not me personally, not me mentally, or me emotionally with anxiety and the stress I had to give that up. And yes, it was a good deal of money that I gave up, but I feel like I had to stop sacrificing the peace in my life for money. And once I let that go, I definitely opened the door for other things to come in. So just have some grace and know that you could have a $10K month, a $20K month. You could have a $3K month. Maybe you're making a thousand dollars a month. And that's amazing for you because you still have a corporate job or. So give yourself some grace. You are probably going to start slow. And that's what happens to pretty much all of us, but you never know when you're going to hit your first $14K month.

But again, I had a $14K month and then like a $12K month and then the $10K month. And then a $3K month where I was like, “Oh, like this isn't going the right way.” So you just can't let that hold you down because I did. But if I gave up, then I wouldn't be here. If I had given up six months ago, then I wouldn't be celebrating one year in business. So you have to hang on and you have to do what it takes to make it work every month, including offering services that maybe you're not obsessed with, but maybe you need to offer those services right now so you can get to the next level so that you can find the right clients for your business. And that's okay because everyone is figuring it out as they go. Even if it doesn't look like it on social media. So just know there's ups and downs that is completely normal. Like I said, I had the highest month of my one year in business and then the lowest month and I was so scared, but I figured it out and things are just going to happen, but you have to stay confident and you have to stay motivated because people can feel that.

And if you go into a sales call or a discovery call and you feel desperate, then the client is probably going to feel that too. And maybe not hire you. So just chill out. It's going to be okay. And you'll figure it out. So that's kind of the no bullshit story of what happened in the last year for my business. And just honestly, I am so freaking grateful. I'm so grateful for this community where I get to share about my business and about my journey. And even share about dating and making friends and all the things.

But I could not have done this without the people in my life, my best friends, the incredible mentors that I've had over the past year, my family and this community that I've been building over the past year. I'm so grateful for every single one of those people. And what's fun is like, I get so many messages. I send a lot of messages. Like, I just freaking love that we get to connect with strangers who become friends and friends we haven't talked to for a while. And we become besties because, you know, things just kind of came full circle. I just love this community and what I want to say to you is again, no matter where you're at in your business, in your career, anything is possible. I truly, truly believe that. So if I'm telling you that it's possible and that you can make this work and be just so freaking happy and feel. More fulfilled than you ever have in your career. I'm saying that because I've experienced this and it's been a wild journey.

I will be honest and say that it hasn't been super easy for me this year. It's been a lot of highs, a lot of lows, but I've learned so much and I'm so excited for what's next for me.I just want to end this episode by saying whatever is in the back of your mind right now, or whatever is giving you the butterflies, like about your career, about a business, about that side hustle, whatever you're toying with right now, I want you to know that it's freaking possible.

And again, I'm not the person who's going to say you're going to make a hundred thousand dollars next month, or let's make you a millionaire by May. Like I'm not that person. I'm the person who's going to say, “Look, this shit was hard for me, but you just heard what I learned, what I went through, and I'm still doing the damn thing.”

I am still running the business. I am growing my business so much in 2024 and I'm going for it because I know it's possible and it's going to be a little bit tough, but that's what happens when you're doing something that you're so freaking excited about that you've never done before. So if that's you, I am here with you. Take one action today or tomorrow that takes you toward your dream, toward happiness, toward fulfillment, because you can make it happen.